Oxygen Radicals in Biological Systems

649 Pages·1984·12.379 MB·English

by  Lester Packer (Eds.)

Methods in Enzymology
Volume 105
Oxygen Radicals in
Biological Systems
EDITED BY
Lester Packer
MEMBRANE BIOENERGETICS GROUP
UNIVERSITY OF CALIFORNIA
BERKELEY, CALIFORNIA
Advisory Board
Bruce Ames Rolf .J. Mehlhorn
Anthony Diplock William A. Pryor
Lars Ernster Trevor F. Slater
Irwin Fridovich
Academic Press
San Diego New York Boston
London Sydney Tokyo Toronto
Contributors to Volume 105
Article numbers are in parentheses following the names of contributors.
Affiliations listed are current.
R. B. ILREKABA (3), lndustrias, ,otnasnoM Cancer Research, Columbia ,ytisrevinU
Estrada Municipal, PLN 393 ,ainiluaP egelloC of snaicisyhP and Surgeons, New
Sdo Paulo, Brazil ,kroY New York 23001
Huoo AEBI (13), sehcsimehc-hcsinizideM OTREBLA SiREVOB (57), Departamento de
lnstitut, tiitisrevinU Bern, 0003-HC Bern acinhuQ Biol6gica, Facultad de Farma-
,9 Switzerland ciay Bioqufmica, dadisreoinU de Buenos
TriED P. M. MOOnREKA (59), Institut fiir Aires, 3111 Buenos Aires, anitnegrA
Physiologische Chemie !, tiitisrevinU M. IRONURB (2), Department of -simehcoiB
,frodlessifD D-4000 Diisseldorf, Federal try, lacigoloiB Sciences, and -nemirepxE
Republic of ynamreG lat Medicine, H University of Rome,
ECURB N. AMES (29, 44), Department of Rome ,00100 Italy
Biochemistry, University of ,ainrofilaC JUDITH L. SSIRTTUB (15), Department of
Berkeley, aiurofilaC 02749 Biochemistry, Guy's Hospital Medical
AlCIRTAP C. SWERDNA (45), Department of School, London SEI 9RT, England
Medicine, Tufts-New England Medical EUQIRNE SANEDAC (26), lnstitut fiir Phy-
Center, Boston, Massachusetts 11120 ehcsigolois Chemie ,I tiitisrevinU -lessiiD
Kozl ASADA (56), ehT Research Institute dorf, 0004-D ,frodlessiiD Federal Repub-
for Food Science, Kyoto ,ytisreviaU ,ijU cil of ynamreG
Kyoto 611, Japan ECNERWAL CASTLE (34), Department of
RETEID-sUALK SUMSA (20), -rentieM-nhaH Chemistry, Louisiana State ,ytisrevinU
lnstitut Berlin, Bereich Strahlenchemie, Baton Rouge, Louisiana 30807
00OI-D Berlbz ,93 Federal Republic of DRAHCIR TRACHTAC (44), Department of
ynamreG Biochemistry, University of ,ainrofilaC
DRANREB M. ROIBAB (45), Department of Berkeley, ainrofilaC 02749
Medicine, Tufts-New England Medical RUHTRA .1 MUABREDEC (68), Department of
,retneC Boston, Massachusetts 11120 Biochemistry, Mount Sinai School of
J. V. RETSINNAB (9), Inorganic yrtsimehC ,enicideM New York, New York 92001
,yrotarobaL ytisrevinU of ,drofxO Oxford LEAHCIM F. NAMTStRHC (29), Department
OXI 3QR, England of ,yrtsimehcoiB ytisrevinU of ,ainrofilaC
W. H. RETSI~mAB (9), Nuffield Department Berkeley, ainrofilaC 02749
of lacinilC Biochemistry, Radcliffe -rifnI SINNED P, CEll:FORD (51), gniraW-bbeW
mary, University of Oxford, Oxford 2XO Lung Institute, University of odaroloC
6HE, England Medical Center, Denver, odaroloC 26208
NONEB H. J. BIELSKI (8), Department of DLAREG NEHOC (36, 67, 68), Department of
,yrtsimehC Brookhaven National -arobaL Neurology, Mount Sinai School of -ideM
tory, Upton, New York 37911 cine, New York, New York 92001
R. P. BIRD (35), Ludwig Institute for Cancer NODIG IKSPAZC (24), Deportment of -isyhP
Research, Toronto, Ontario M4Y 2L4, lac Chemistry, Hebrew ytisrevinU of Je-
adanaC ,melasur Jerusalem ,40919 Israel
AIMRAC KEROB (62), lacigoloidaR Research ODNALOR EED ORTSEAM (49), Brain Re-
,yrotarobaL Cancer Center, Institute of search Laboratory, Department of -inilC
xi
xii CONTRIBUTORS TO VOLUME 105
cal Neurological Sciences, Victoria Hos- Western Reserve University, Cleveland,
pital, London, Ontario N6A 4G5, Canada Ohio 44106
TIJARDNI D. (16), DESA! Division of Human AKINOM J. (1), GREEN Inorganic Chemisto,
Nutrition, University of British Cohtmbia, Laboratory, University of Oxford, Oxford
Vancouver, British Columbia V6T I ,5W OXI 3QR, England
Canada CNAG~LOW A. GONZLER (12), Gdinenthal
AROC J. (41), DILLARD Department of Food GmbH, Center of Research, OOM-D
Science and Technology, University of Aachen, FederRaelp ublic of Germany
Cal(fornia, Davis, California 61659 JOHN M. C. (4), GUTTERIDGE National In-
YNOHTNA T. KCOLPID (15), Department of stitute for Biological Standards, Hamp-
Biochemistry, Guy's Hospital Medical stead, London HW3 6RB, England
School, London SEI 9RT, England YRRAB (4), HALLIWELL Department of Bio-
SAMOHT A. DIX (43), Department of Chem- chemistry, King's College, University of
istry, Pennsylvania State University, London, London WC2R 2LS, England
State College, Pennsylvania 20861 HOSNi M. HASSAN (30, 53, 69), Depart-
H. H. (35), DRAPER Department of Nutri- ments of Food Science and Microbiology,
tion, University of Guelph, Gaelph, On- North Carolina State University, Raleigh,
tario NIG 2WI, Canada North Carolina 27650
NNAMREH BEOABRETSE (38), Institute of LINDA HATCH (19), Institute for Toxicol-
Biochemistry, University of Graz, A-8010 ogy, University of Southern California,
Graz, Austria Los Angeles, California 33009
L. ~iHOLF (10, 12), Griinenthal GmbH, Cen- UMASO HAYAISm (6), Osaka Medical Col-
ter of Research, OOM-D Aachen, Federal lege, Takatsuki 569, Japan
Republic of Germany DRAHCIR E. HEmKILA (67), Department of
TREBOR A. (27), FLOYD Biomembrane Re- Neurology, Rutgers Medical School, Pis-
search Program, Oklahoma Medical Re- cataway, New Jersey 45880
search Foundation, Oklahoma City, H. ALLEN O. HILL (1), Inorganic Chemistry
Oklahoma 40137 Laboratory, University of Oxford, Oxford
REHPOTSmHC S. (3), FOOTE Department of OXI 3QR, England
Chemisoy, University of California, Los PAUL NIETSHCOH (19), Institute for Toxicol-
Angeles, California 42009 ogy, University of Southern California,
L. G. FORm (21), Department of Biochemis- Los Angeles, California 33009
try, Brunel University, Uxbridge UB8 MONiC^ HOLLSTEIN (29), Department of
3PH, England Biochemistry, University of California,
IRWIN (5), FRIDOWCH Department of Bio- Berkeley, California 94720
chemistry, Duke University Medical Cen- UROTAS AYONEKI (17), Development Divi-
ter, Durham, North Carolina 27710 sion, Eisai Co., Ltd., Koishikawa, 4-6-10
CrlERYL A. FORTEK (31), Laboratories of Bunkyo-ku, Tokyo, Japan
Molecular Biology and Genetics, Univer- KENDALL A. OKOT1 (42), Medical School,
sity of Wisconsin, Madison, Wisconsin Health Science Center, University of Mis-
60735 souri, Columbia, Missouri 11256
ECORB L. GELLER 1( I), Department of Bio- YRRAH S. BOCAJ (48), Division of Hematol-
logical Chemistry, UCLA School of Medi- ogy, Mayo Memorial Building, University
cine, Los Angeles, California 42009 of Minnesota Hospitals, Minneapolis,
Emc A. GLENDE, JR. (40), Department of Minnesota 55455
Physiology, School of Medicine, Case DRAWDE G. (22), JANZEN Guelph-Waterloo
CONTRIBUTORS TO VOLUME 105 XII! °.°
Center for Graduate Work ni ,yrtsimehC chemistry, ytisrevinU of ,ukruT 00502-FS
Department of yrtsimebC and -simehcoiB ukruT ,05 Finland
try, University of Guelph, Guelph, -nO W. NNAMHOL (60), lnstitut fiir ,kisyhpoiB
oirat NIG 2WI, adanaC ,tiitisreuinU-gibeiL-sutsuJ D-6300 Gies-
RICHAnD B. ,NOTSNHOJ JR. (46), Depart- Republic sen, Federal of ynamreG
ment of ,scirtaideP Hos- Jewish National J. WILLIAM LOWH (70), Department of
pital and Research Center, and -revinU ytisrev i,nyUrtsimehC of Edmon- Alberta,
sity of Colorado School of Medicine, ton, Alberta G6T Canada 2G2,
Denver, odaroloC 60208
MICH[LE TREKRAM (45), Cen- Laboratoire
DLORAH P. SENOJ (50), Department of -oiB lart de Chimie ,eaqinilC Centre -atipsoH
chemistry, University of Alabama, South lier Unioersitaire Vaudois, 1011 Lau-
,eliboM Alabama 88663 sanne, Switzerland
KouIcHI AMAYATAK (17), Tsukuba Re- ECNERWAL J. TTENRAM (43, 54), -trapeD
Eisai Laboratories, search Co., Ltd., -oT ment of Chemistry, Wayne State -revinU
kodai, Toyosato-machi, Tsukuba-gun, sity, Detroit, Michigan 20284
lbaragi ,62-003 Japan
DLANOR P. NOSAM (55), Laboratory of -oM
RUOMYES J. (52), KLEnANOFF Department ralucel Biophysics, National Institute of
of Medicine, University of notgnihsaW Enviromnental Health Sciences, Re-
School of Seattle, Medicine, notgnihsaW search Triangle Park, North aniloraC
59189 90772
NAMRON .1 YKSNIRK (18), Department of Joe M. DROCCM (50), Department of -oiB
Biochemistry and Pharmacology, Tufts chemistry, University of South Alabama,
ytisrevinU School of Medicine, Boston, ,eliboM Alabama 88663
Massachusetts 1120 !
ROLF J. NROHLHEM (25), Membrane -neoiB
OMIS OSKAAL (14), Department of -mehcoiB ,puorG scitegre Labo- Berkeley Lawrence
istry, University of Turku, 00502-FS ,yrotar ytisrevinU of ,ainrofilaC Berkeley,
ukruT ,05 Finland ainrofilaC 02749
ANNAHOJ (38), LANG Institute of -mehcoiB WERDNA R. LATZSKIM (7), Department of
istry, University of Graz, A-8010 ,zarG yrtsimehC and yrtsimehcoiB and -uceloM
airtsuA ral Biology Institute, University of -ilaC
GLEN D. ECNERWAL (36), Institute of -uH fornia, Los Angeles, ainrofilaC 42009
Nutrition, matt Columbia ytisrevinU -loC YROGERG V. (42), MILLER Medical ,loohcS
lege of Physicians and Surgeons, New Center, Science Health ytisrevinU of -siM
,kroY New York 23001 ,iruos Missouri Columbia, 11256
NEHPETS A. (71), LESKO Division of -oiB SELRAHC F. WODLOM (48), Department of
physics, ehT Johns Hopkins ytisrevinU ,enicideM Veterans noitartsinimdA -ideM
School of Hygiene and Public Health, lac Center, Minneapolis, Minnesota
,eromitlaB Maryland 50212 71455
DIVAD E. LEVlN (29), Department of -oiB ALLEMRAC S. YDOOM (30), Department of
chemistry, University of ,ainrofilaC ,ygoloiborciM North aniloraC State -inU
Berkeley, ainrofilaC 02749 ,ytisrev Raleigh, North aniloraC 05672
C. NNA LEWIS (27), Department of -oiB NIMRA RELLOM (37), fiir lnstitut -oloisyhP
chemistry and ,ygoloiborciM ytisrevinU gische Chemie ,1 tiitisrevinU ,frodlessiiD
of St. Andrews, St. Andrews Fife Ky16 0004-D Diisseldorf, Federal Republic of
9AL, Scotland ynamreG
EsA-MATrl (14), LILIUS Department of -DiB HTENNEK D. SERK4rUM (31), seirotarobaL
xiv TO VOLUME CONTRIBUTORS 105
of Molecular Biology and Genetics, Uni- Institute, University of Colorado Medical
versity of Wisconsin, Madison, Wisconsin Center, Denver, Colorado 26208
60735 HPOTSlRHC RICHTER (58), Laboratory of
H. REHCABOEN (60), lnstitut flit Biophysik, Biochemistry ,1 Swiss Federal Institute of
Justus-Liebig-Universitiit, D-6300 Gies- Technology, CH-8092 Ziirich, Switzer-
sen, Federal Republic of Germany land
YRRAL W. YELREBO (61), Radiation Re- DLAREG M. ROSEN (23), Department of
search Laboratory, Department of Radi- Pharmacology, Duke University Medical
ology, The University of lowa, Iowa Oty, Center, Durham, North Carolina 27710
Iowa 24225 YRNEH NESOR (52), Department of Medi-
RETEP J. O'BRIEN (47), Department of Bio- cine, University of Washington School of
chemistry, Memorial University of New- Medicine, Seattle, Washington 59189
foundland, St. John's, Ne~foundland G. ROTILIO (2), Department of Biology,
AIB 3X9, Canada Faculty of Sciences, H University of
NETS SUINERRO (66), Department of Foren- Rome, Rome Italy 00100,
s& Medicine, Karolinska lnstitutet, S-104 DLANOD T. (7), SAWYER Department of
lO Stockhohn, Sweden Chemistry, University of California, Riv-
F. 6TTING (It)), Grtinenthal GmbH, Center erside, Riverside, California 12529
of Research, D-5100 Aachen, Federal Re- SREIWHCS HTEBAZILE (44), Department of
public of Germany Biochemistry, Unwersity of California,
RETSEL REKCAP (25), Membrane Bioenerge- Berkeley, California 94720
tics Group, University of California, REGOR C. YLAES (63), National Biomedical
Berkeley, California 94720 ESR Center, Medical College of Wiscon-
DLANOR 3CIHTEP (28), School of Electronic sin, Mihvaukee, Wisconsin 53226
~gnireenignE Science, University College XELA NAINAVES (19), Institute for Toxicol-
of North Wales, Bangor, Gwynedd LL57 ogy, University of Southern California,
IUT, Wales Los Angeles, California 33009
NED A. RETROP (32), Department of Chem- F. C. KOOHS (3), Pilot Chemical Company,
istry, Duke University, Durham, North Santa Fe Springs, California 90670
Carolina 27706 PAUL H. (54), SIEDLIK Pharmacology De-
MAILLIW A. ROYRP (34), Departments of partment, Warner Lambert-Parke Davis,
Chemistry and Biochemistry, Louisiana Ann Arbor, Michigan 48105
State University, BatonR ouge, Louisiana TUMLEH SIES (26, 37, 59), Institutfiir Phy-
30807 siologische Chemie ,1 Unioersitdt Diisseb
REMLE J. NAMKCUAR (23), Department of dorf, Diisseldorf, D-4000 Federal Repub-
Surgery, Duke University Medical Cen- lic of Germany
ter, Durham, North Carolina 27710 T. F. RETALS (33, 38), Deparonent of Bio-
DRAHCIR O. LEGANKCER (40), Department chemistry, Brunel University, Uxbridge,
of Physiology, School of Medicine, Case Middlesex UB8 3PH, England
Western Reserve University, Cleveland, NVTRAM T. SMITH (66), Department of
Ohio 60144 Biomedical and Environmental Heahh
J. LESLIE HTAPDER (65), Division of Radia- Sciences, University of ,ainrorOlaC Berke-
tion Oncology, Department of Radiologi- ley, California 94720
cal Sciences, California College of Medi- R. S. LAHOS (64), Department of Biology,
cine, University of California, Irvine, Southern Methodist University, Dallas,
California 92717 Texas 57257
NHOJ E. REPINE (51), Webb-Waring Lung SALGUOD R. SPITZ (61), Radiation Re-
TO CONTRIBUTORS VOLUME 10~ VX
search Laboratory, Department of -idaR RAKAHDUS RAWIKNALEW (18), Department
,ygolo ehT ytisrevinU of Iowa, lowa ,ytiC of yrtsimehcoiB and ,ygolocamrahP Tt~s
Iowa 24225 ytisrevinU School of Medicine, Boston,
Massachusetts 11120
MAILLIW S. KRATS (42), noisiviD of -igoloiB
lac Sciences, University of ,iruossiM -oC R. L. WlLLSON (21), Department of -oiB
,aibmul Missouri 11256 chemistry, Brunel University, egdirbxU
8BU 3PH, England
ORIHASAM ADAKAT (I 7), Research Tsukuba
,seirotarobaL Eisai Co., Ltd., ,iadokoT SINNED R. EGN1W (11), Departments of .oiB
chemistry and Medicine, University of
,ihcam-otasoyoT Tsukuba-gun, lbaragi
Utah, Salt Lake City, Utah 23148
,62-003 Japan
RETEP K. WONG (27), Biomembrane Re-
ALL. TAPPEL (41), Department of Food
Re- Medical Program, Oklahoma search
Science and Technology, University of
search Foundation, Oklahoma City,
,ainrofilaC Davis, ainrofilaC 61659
amohalkO 40137
SIDROJH (66), THOR Department of cisneroF
KUNIO 1GAY (39), Institute of Applied -oiB
,enicideM Instituter, S-!04 Karolinska 1O
chemistry, Yagi Park, Mitake, Memorial
Stockholm, Sweden
~ifiG Japan 505-I,
AKKEP NENURUT (14), Biochemical Wallac ORATOYR YOSHIDA (6), Department of
,yrotarobaL 10102-FS Turku ,01 Finland Medical Chemistry, Kyoto University
NAOJ S. (7), VALENTINE Department of Faculty of ,enicideM Kyoto ,606 Japan
yrtsimehC and Biochemistry and -uceloM IKAURET YUZURIHA (17), Tsukuba Re-
ral Biology Institute, University of -ilaC search ,seirotarobaL Co., Ltd., Eisai -oT
fornia, Los Angeles, ainrofilaC 42009 kodai, Toyosato-machi, Tsukuba-gun,
NNA M. HPRODSRETLAW (52), Department igarabI ,62-003 Japan
of Medicine, University of notgnihsaW AIVLYS CEVARDAZ (38), Institute of -oiB
School of Medicine, Seattle, notgnihsaW chemistry, University of Graz, 0108-A
59189 ,zarG Austria
Preface
Increasingly, researchers and clinicians are recognizing that biological
damage mediated by reactive species of oxygen is an important factor in
disease and aging. Oxygen radical damage has been implicated in inflam-
mation, arthritis, adult respiratory distress syndrome, myocardial infarc-
tion, pulmonary dysfunction in hemodialized patients, Purtscher's syn-
drome, Bloom's syndrome, systemic lupus erythematosus, mutagenicity
and carcinogenicity, and other pathologies. While more experimental data
to support the involvement of oxygen radicals in these conditions are
needed, the explosive interest of many investigators in the field more than
warrants a volume that covers the most current methods used in studying
the role of oxygen radicals in biological systems.
Much of the recent progress in research concerning the role of oxygen
radicals in disease has been due to the discovery and utilization of antioxi-
dant substances. Since the discovery by McCord and Fridovich that the
plasma protein, erythrocuprein, functions to dismutate the superoxide
anion radical, this oxygen radical, as well as other oxygen radical species
and products derived therefrom, have received a great deal of attention.
These other compounds include hydrogen peroxide, hydroxyl radical
(OH .), and singlet oxygen .)2O~( The study of oxygen radical reactions in
simple chemical and biochemical systems has defined parameters govern-
ing the initiation, propagation, and termination of destructive free radical
chain reactions, and this understanding has suggested oxygen radical in-
volvement in a remarkably diverse and extensive array of pathological
states.
Dramatic therapeutic effects of antioxidant substances, such as vita-
min E and selenium, in clinical settings have provided further support for
the involvement of oxygen radicals in certain disease conditions. Recent
research results of chemists, biologists, clinicians, and epidemiologists
have created a new multidisciplinary field considered by some to be
among the most exciting and important areas of biological research.
As with most research, progress is frequently accelerated by the publi-
cation of a single volume that contains all of the state-of-the-art methodol-
ogies used in the field. The major emphasis of this volume is on the
methods and on the basic chemistry and biochemistry of oxygen radicals
and their effects in biological systems. Such a volume, it is hoped, will
stimulate new research, heighten awareness of recent discoveries in basic
research, and focus attention on their implications for human health.
In preparing this volume, I would be remiss in not pointing out the
very great benefit derived from the active participation of the advisory
xvii
XVill °°° PREFACE
board (Bruce Ames, Anthony Dipiock, Lars Ernster, Irwin Fridovich,
Rolf J. Mehlhorn, William A. Pryor, and Trevor Slater) and Ai L. Tappel
in the selection of the methods to be included and in identifying the
leading investigators to make these contributions to the volume. Also I
acknowledge the valuable editorial and administrative assistance pro-
vided by Mr. John Hazlett who worked closely with me in bringing this
volume to fruition.
LESTER PACKER
METHODS IN ENZYMOLOGY
EDITED BY
Sidney P. Colowick and Nathan O. Kaplan
VANDERBILT UNIVERSITY DEPARTMENT OF CHEMISTRY
SCHOOL OF MEDICINE UNIVERSITY OF CALIFORNIA
NASHVILLE, TENNESSEE AT SAN DIEGO
LA JOLLA, CALIFORNIA
I. Preparation and Assay of Enzymes
II. Preparation and Assay of Enzymes
III. Preparation and Assay of Substrates
IV. Special Techniques for the Enzymologist
V. Preparation and Assay of Enzymes
VI. Preparation and Assay of Enzymes )deunitnoC(
Preparation and Assay of Substrates
Special Techniques
VII. Cumulative Subject Index
xix
METHODS IN ENZYMOLOGY
EDITORS-IN-CHIEF
Sidney .P Colowick Nathan .O nalpaK
EMULOV VIII. Complex Carbohydrates
Edited yb ELIZABETH F. NEUFELD AND VICTOR GINSBURG
EMULOV IX. Carbohydrate Metabolism
Edited yb SILLIW A. DOOW
EMULOV X. Oxidation and Phosphorylation
Edited yb DLANOR W. KOORBATSE DNA DRANYAM E. NAMLLUP
EMULOV XI. Enzyme Structure
Edited yb C. H. W. SRIH
EMULOV XII. Nucleic Acids (Parts A and )B
Edited yb LAWRENCE AND GROSSMAN KIVIE MOLDAVE
EMULOV XIII. Citric Acid Cycle
Edited yb J. M. NIETSNEWOL
EMULOV XIV. Lipids
Edited yb J. M. NIETSNEWOL
EMULOV XV. Steroids and Terpenoids
Edited yb DNOMYAR B. NOTYALC
EMULOV XVI. Fast Reactions
Edited yb HTENNEK NITSUK
EMULOV XVII. Metabolism of AminoA cids and Amines (Parts A and B)
Edited yb HERBERT TABOR AND CELIA WHITE TABOR
EMULOV XVIII. Vitamins and Coenzymes (Parts A, B, and C)
Edited yb DLANOD B. MCCORMICK AND LEMUEL D. WRIGHT
EMULOV XlX. Proteolytic Enzymes
Edited yb EDURTREG E. NNAMLREP DNA OLZSAL DNAROL
ixx